


Babyface

by darkdragonhorde



Category: Supernatural
Genre: Age Difference, Anal Fingering, Blow Jobs, Comeplay, Coming Untouched, Dead Dove: Do Not Eat, Don't Try This At Home, Drugged Sex, F/M, Facials, Forced Orgasm, Gangbang, M/M, Multi, Non-Consensual Blow Jobs, Rape/Non-con Elements, Rimming, Size Difference, Succubi & Incubi, Twink Dean, Unsafe Sex, brief m/f sex, possible impregnation
Language: English
Status: Completed
Published: 2018-06-20
Updated: 2018-06-20
Packaged: 2019-05-25 19:38:43
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 6,395
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14984150
Author URL: https://archiveofourown.org/users/darkdragonhorde/pseuds/darkdragonhorde
Summary: Babyfaced Dean Winchester finally gets a night all to himself. John is hunting, Sam is away at Stanford, and Cassie told him to get the fuck out of her life. Things are good, he's a free man.Everything is coming up roses until a pool hustling trip at a divebar goes sideways and Dean ends up fucked six ways from Sunday. Whatwasin those shots, anyway? He makes a bet with his captors for his freedom, can he hold out against their wandering fingers and tongues?





	Babyface

**Author's Note:**

> Oh man... I've never finished writing a dark fit before and I've certainly never shared one. Heed this warning: there be rape in here. 
> 
> Don't like? The back button should be at the top of your page.

Dean was a free man tonight. His dad was off on a hunting trip. His younger brother was still refusing to return his calls while he lived the high life at Stanford. And Cassie thought Dean was a lunatic, so he was officially single again. 

It was good to be free.

Armed with some seed money to fund his pool table hustling, Dean strutted into a dive bar named _Lou’s_ and sized up the room. There were a few big guys standing at the bar looking Dean up and down in a way that made the hair on the back of his neck stand on end. Looking past them showed the typical dive bar regulars: Several pretty women who watched Dean like they wanted to take him home and corrupt him; some rough and tumble guys in work clothes pounding down a drink or two before heading back to their home lives; and then there were the scattered alcoholics that would beg, barter, and steal to keep their regular spot in the bar occupied and the drinks flowing their way.

Dean swallowed around the lump in his throat and pasted on an easy smile, one he’d seen on John’s face thousands of times over the years. It didn’t matter that he was on his own tonight and without backup should anything go wrong, he could handle anything. He made his way to the bar and ordered a beer. The gruff man behind the counter studied Dean’s driver’s license like there’d be an exam later. 

“You sure babyface there is old enough for a drink, Lou?” one of the big guys at the bar asked. 

“Yeah, he’s legal,” Lou said as he wiggled Dean’s driver’s license between two fingers before handing it back to Dean. “Coulda fooled me though. Kids look younger and younger every year.”

“That’s cause you’re getting old, man,” another big guy said. He came around to sit on the stool to Dean’s left as his friend settled onto the one to Dean’s right. “Lemme guess, you’re out celebrating your twenty-first birthday by yourself?”

Dean scowled at the man as he accepted his beer. “I’m twenty-three.”

The man’s blond eyebrows raised and he pursed his lips. 

“My apologies. Looks like you’re not the only one getting old here, Lou.” He held out one of his meaty hands. “Name’s Al. How about I buy the next round to make up for the mistake?”

Dean did a little math to figure out how much extra cash he had to get himself looking tipsy enough to pull off the night’s hustle. He was a little light. His easy smile returned as he shook Al’s hand. “You’ve got yourself a deal.”

A large, solid hand landed on Dean’s left shoulder. He silently praised himself for not jumping at the touch and he looked over his right shoulder to see Al’s friend. The man had salt and pepper hair and clear blue eyes. His skin creased around his eyes as he smiled at Dean. 

“I’ll buy the round after that if you’re game,” he said. “You can call me Eddie.”

“Nice to meet you, Eddie. I’m Dean.”

“At least you have a solid, man’s name to go with that babyface,” Al said. 

“Leave him be,” Eddie said. He still hadn’t let go of Dean’s shoulder and seemed to have moved closer. Close enough that Dean could feel Eddie’s body heat along his back. “He can’t help the way he looks. ‘Sides, you know you’re jealous you didn’t have his looks when you were twenty-three. I bet the ladies love him.”

“There’s an idea,” Al said. He waved Lou down and whispered his order over the bar. While Lou prepped the drinks, Al leaned against the bar with his bottom lip caught between his teeth. He glanced at Dean and Eddie before looking past them at the other people in the bar. “Why don’t we see how those lovely ladies over there feel about babyface here?”

Lou slid a tray of shots onto the bar. Al grinned at him as he picked up the tray and nodded at Eddie and Dean to follow. Eddie used his hold on Dean’s shoulder to turn him around. His hand smoothed over the back of Dean’s shoulders. Dean could have sworn he’d felt Eddie’s thumb brush purposefully over the base of Dean’s skull on its way to rest over Dean’s right shoulder. Dean looked up at Eddie in confusion. 

“Come on, Dean,” Eddie said as he leaned close enough to whisper in Dean’s ear. “Let’s go make sure you’ll get your dick wet tonight.”

A shiver ran down Dean’s spine and he nodded. Getting laid was better than hustling pool any night.

Al and Eddie introduced Dean to a group of older women who Dean had dismissed earlier as being merely pretty, but were actually beautiful up close. A dark haired woman named Roberta with whiskey colored eyes took a shine to Dean early on. He didn’t know what kind of perfume she was wearing, but the way it mixed with the scent of the bar and the shots Eddie kept pushing into Dean’s hands was making Dean all kinds of hard in his jeans and hot under the collar. 

The passage of time was hard to follow in the bar. Dark windows obscured the world outside and hardly anyone else came in after Dean had. Not that he noticed anyway. He might have missed a thing or two thanks to Roberta’s wandering hands and her blonde friend Shelly’s constant need to kiss him. Hours must have passed with him pressed between the two women. They traded kisses, felt each other up, and took turns doing body shots off of each other’s pulse points, cleavage, and Dean’s clavicle. 

He didn’t know when time started to jump on him either. He didn’t know when the little table in their booth was pulled back to make room for Roberta and Shelly to kneel at his feet. Or when they’d undone his fly and pulled out his cock. 

He became aware of these things around the same time that he realized Al was holding Dean’s forearms together while Eddie wrapped Dean’s belt around Dean’s wrists. Any protesting Dean wanted to make died on his lips as Roberta took Dean’s cock into her mouth and swallowed him down until her nose was pressed to his pubic bone. He vaguely felt it when the back of his head slammed back against the booth where he sat. 

Shelly disappeared sometime after she’d had Dean sucking on her nipples while someone—Roberta? Eddie?—held Dean’s cock up to tease against the wet folds of her pussy. 

Dean was pretty sure the first time he came that night was with his cock buried deep inside Roberta’s pussy with her tits in his face. He was also pretty sure that Eddie and Al were sucking marks into his neck by that point. Eddie’s beard and Al’s sandpaper five o’clock shadow left dueling trails of scratching heat on the sensitive skin of Dean’s neck. Scratches that they soothed over with their tongues and lips. 

Time went blurry again after that. The next time Dean came around he was naked and stretched out on a lumpy bed somewhere with his wrists tied to a headboard. Someone was sucking his cock. It felt like Eddie, judging by the prickling of the beard against his balls when the person sucking him took him deep. 

“There you are,” Al said from somewhere on Dean’s right. “You’re doing so well, babyface. I’m so proud of you.”

Something wet and solid nudged at the skin below Dean’s balls. He grunted and tried to pull away from the touch. It didn’t matter how good Eddie’s mouth felt or how often Dean had secretly watched other guys changing before wrestling practice back in school, he wasn’t gay. 

“Now, now, none of that,” Al said as he settled onto the bed next to Dean and grabbed a handful of Dean’s hair. “Eddie’s doing a lot of work to make you feel good, babyface. It’s rude to refuse the favor.”

Eddie hummed around Dean’s cock as his finger started to push at Dean’s hole. 

Dean tried to shake his head, but Al held him steady by the hair. Dean blinked up at Al with stinging eyes. When had he started crying? “Please, don’t do this.”

Al trailed the fingers of his unoccupied hand over Dean’s chest. His blunt fingernails scraped over one of Dean’s nipples. Dean’s eyes slammed shut and he fought to keep from making any noise. Al’s attention seemed to hone in on Dean’s nipples. Over and over he scratched at the sensitive skin around them and over the nubs themselves. As Eddie began to work his thick finger into Dean’s ass, Al pinched Dean’s oversensitive nipple between two fingers and rolled the skin. 

Dean’s mouth fell open in spite of himself. He couldn’t hold back the moan that escaped his lips. He couldn’t tell if it was from pleasure or pain. Al’s hold on Dean’s hair tightened as Al switched his attention to Dean’s other nipple. Eddie began to slowly pump his finger in and out of Dean’s ass. 

“Fuck, you look good like this,” Al said. “I knew you would.”

A door opened across the room. Light blinded Dean for a moment before disappearing as the door clicked shut. 

“I hope you’ve saved some for me,” Lou the bartender said. Dean could hear the man’s belt jingle as he started to strip. Al beamed down at Dean as he used Dean’s hair to tip Dean’s head back. 

“As promised, you get first dibs at his mouth,” Al said as he stared into Dean’s eyes. 

“Good,” Lou said. Dean felt the bed dip under Lou’s weight on his left. He stared up into Al’s eyes, pleading silently. A soft, old hand settled on Dean’s right cheek as Lou started to turn Dean to face him. “You can let him go, Al. I can handle those cocksucker lips for now.”

Al released Dean’s hair and patted him on the forehead like Dean was a dog who’d just rolled over for a treat. Dean pressed his lips together as Lou’s bare, leaking cock came into view. 

Lou tsk-ed. “None of that.”

Lou let go of Dean’s cheek and grabbed hold of Dean’s nose, pressing his nostrils closed as he shuffled closer to Dean’s face. Dean’s eyes watered as he fought against the urge to open his mouth to take in air. Just as the world started to dim around the edges, Eddie worked another finger into Dean’s ass. 

Dean cried out.

A cry that was muffled by Lou’s cock almost as soon as Dean had started making noise. Lou’s cock was thankfully clean and tasted only of slightly salty skin as it began to plunge in and out of Dean’s mouth. 

Eddie’s fingers curled inside Dean’s ass, nailing his prostate and making Dean groan. 

“That’s it, babyface,” Al said as he leaned in to kiss Dean’s shoulder then his collarbone and the skin between his pecs. “Let us make you feel good. Make us feel good in return, too.”

Dean’s protests didn’t make much of a difference when they were voiced around Lou’s cock. 

Al’s tongue swiped over Dean’s right nipple and Dean froze. Al laughed against Dean’s skin before licking Dean’s nipple again and again. Eddie continued to press his two fingers against Dean’s prostate while he sucked Dean’s cock deep. Lou cradled the back of Dean’s head while he sunk his own cock into Dean’s mouth over and over. 

Something was building inside Dean. It tightened and tensed and grew more and more apparent as the three men used Dean’s body. When Al took Dean’s nipple between his teeth and flicked his tongue over the tip, it was like the world ended. Dean’s orgasm hit him harder than he’d felt in years. He came and he came and Eddie swallowed it all down. None of the men let up on their attention as Dean cried out around Lou’s cock. 

Dean was dimly aware of Lou grunting before Dean’s mouth was flooded with Lou’s hot cum. Lou pulled out after Dean had unwillingly swallowed about half of his load. He watched with disassociated interest as Lou stroked his cock and shot the rest of his cum onto Dean’s cheeks, chin, and swollen lips. 

When Eddie finally let Dean’s cock slip from his mouth with an audible pop, Dean felt like every muscle in his body was going to melt like a some Saturday morning cartoon character. Eddie was gentle when he pulled his fingers from Dean’s ass and Al finally left Dean’s nipples alone for more than five seconds. 

Al stretched out against Dean’s right side. He slung one leg over Dean’s right knee and hooked his ankle against Dean’s right calf. Eddie’s knees were still pressed between Dean’s thighs.

“I needed that.” Lou moved off the bed with a drawn out sigh. “Make sure to clean up and lock everything up when you’re finished.”

Without waiting for a response Lou left the room.

“Told you he’d be a natural,” Al said as he scooped up a finger full of Lou’s cum from Dean’s cheek and wiped it on Dean’s tongue. 

Eddie hummed as he braced on hand on the bed beside Dean’s head and looked Dean over. Eddie’s lips were red and swollen and slick with saliva. There was a heat in his eyes that said he was nowhere near finished for the night. “You were so right.”

“Please, let me go,” Dean said as he stared into Eddie’s eyes.

Eddie frowned. 

“Hey now, that’s no way to show your gratitude for the way we’ve helped you tonight,” Eddie said as he settled down on his elbow. The hair on his chest tickled over Dean’s sensitive nipples. Eddie’s hard cock pressed against the inside line of Dean’s hipbone. Al rolled his hips so Dean could feel Al’s hard cock against the outside of his other hip. Eddie leaned close to Dean’s face and licked a streak of cum from Dean’s cheek. His lips brushed against Dean’s skin as he spoke. “We’re just getting started, babyface.”

“Come on, Eddie,” Al said with a whine. “I want to watch you rail this twink already.”

“No, please,” Dean said, shaking his head. There was no way his ass was stretched enough to take a cock as big as Eddie’s felt. Neither was his mouth. “You can let me go. I won’t tell anyone what happened. I’ll leave town and you’ll never have to see me again. You don’t have to do this.”

Eddie narrowed his eyes. “Your voice is sounding real rough there, babyface. Al, why don’t you get our boy here something to drink?”

Al untangled himself from Dean’s side and moved away from where Dean could feel or see him. Eddie continued to study Dean from a few inches away. He used his fingers and, sometimes, his lips to rub the rest of Lou’s cum into Dean’s skin. 

Dean closed his eyes and did his best to pretend he was elsewhere.

Eddie brushed his thumb over Dean’s bottom lip and moaned deep enough that Dean could feel the rumble in his chest where their bodies were pressed together. 

“Oh, the things I could do to you,” Eddie said. “The things I could make you feel. The noises you would make under my fingers, my tongue… while hanging off the end of my cock. You sure you want me to let you go?”

“Yes,” Dean said. His voice sounded weak and rough even to his own ears and his eyes stung again. Shame burned his cheeks from the inside out. 

“How is our boy doing?” Al asked as he returned. 

Eddie caressed Dean’s cheekbone. “He needs something to drink.”

“I bought some water,” Al said. “Help me get him up.”

Together, the two men untied Dean’s wrists from the headboard and manhandled him until he was sitting with his back to Al’s chest and his legs stretched out across the bed. Eddie was back to kneeling between Dean’s legs, but being upright and untied was an improvement, even if Al’s muscular arms were wrapped around his waist in a mock lover’s hold that was clearly a threat. 

Eddie opened the bottle of water, the cap crackling as he broke the seal, and handed it over. Dean knew he shouldn’t take more drinks from Eddie, whatever was in those shots earlier must have been drugged, but a sealed bottle of water was as safe as he could get right now. Especially considering the fact that whatever they’d given him earlier left his legs feeling like uncooperative noodles.

Dean drained the water bottle and handed it back to Eddie.

“Can I go now?” Dean asked.

Eddie put the lid back on the bottle and tossed it away from the bed. He looked over Dean’s shoulder at Al. Dean glanced between them. They were having some kind of silent conversation that Dean couldn’t follow. 

“You did do everything we asked,” Eddie said. His shoulders slumped and he settled back on his heels. His cock had softened a bit, but still looked huge from Dean’s perspective. 

“And then some,” Al said.

Eddie’s cock twitched as the man nodded in agreement. 

Dean’s tongue felt heavy in his mouth. His pulse picked up as he studied the line of Eddie’s cock resting against the man’s meaty thigh. 

Al started to trace absent patterns against Dean’s torso. 

“It would be rude to ask for more,” Eddie said. He glanced at Dean before looking around the room. 

Al’s hips shifted until Dean became aware of Al’s hard cock pressed against Dean’s lower back. A slick trail of precome painted over Dean’s skin. 

The air in the room seemed to grow hotter, heavier somehow as Dean’s cock began to harden again. He blinked slowly. 

“It would be rude to point out that Eddie gave you an incredible orgasm and didn’t get to come himself,” Al said in a low voice, his lips brushing against the shell of Dean’s ear. The touch sent shivers over Dean’s skin. “Look at him, Dean.”

Dean looked.

Eddie’s cock twitched again. Lifting a bit as it filled and hardened. His balls were tight to his body, his nipples taut on his chest. Eddie’s eyes were hooded as they stared at Dean’s still naked body. Eddie’s lips were still swollen from where he’d sucked Dean’s cock down to the root.

“Don’t you want to help him feel good too?” Al asked. 

Dean whined in the back of his throat. His hips rolled forward in spite of himself as he felt himself nodding in agreement. 

“Don’t you want to feel his big cock stretching you open, filling you up?” Al’s voice was deep and rough like good sex. 

For the first time in Dean’s life, he became aware of how empty his ass felt. The way Eddie’s fingers had moved inside him, had curled against his prostate, had felt really damn good. A cock could feel the same way, right?

“Eddie,” Al said. “I think our boy wants to help you out. Isn’t that right, babyface?”

Dean nodded. Why was he nodding? Why did he feel so empty? Why did it feel like he’d die if he didn’t get Eddie inside him in the next five minutes?

“What the fuck did you guys do to me?” Dean asked as he rolled his hips forward and spread his legs. 

“Nothing much,” Al said.

Eddie grabbed a bottle of lube and wet his fingers. He reached for Dean’s hole again and pushed one, then two fingers inside. Dean’s head fell back against Al’s shoulder.

Al pressed kiss after kiss along the curve of Dean’s neck while Eddie’s fingers thrust in and out of Dean’s ass. A third finger nudged at Dean’s hole, drawing a groan from deep in Dean’s chest. It sunk into him as Al sucked on Dean’s pulse point.

“Seriously,” Dean said, gasping. “You did something to me. Drugged me.”

“Oh, that.” Al laughed against Dean’s jawline. “I suppose we did. Well, the first time it was Roberta and her wife. Roberta’s a succubus and her wife is an incubus. They’ve been trying to have a baby for ages and they feed on tourists in hopes that one day they’ll get lucky. Maybe they got lucky tonight and you’ll be a daddy. What do you think, babyface, you ready to be a daddy?”

Dean shook his head. 

Eddie pulled his fingers from Dean’s ass and slicked up his cock. Eddie leaned forward so he could kiss Al as he pressed the head of his huge cock against Dean’s hole. Dean was trapped between the two large men as they kissed when Eddie began to push his way into Dean’s ass. 

Dean reached up and dug his fingers into Eddie’s shoulders. The sensation of the cock pushing into him was so overwhelming that he didn’t know if he wanted to push Eddie away or pull him closer.

Eddie and Al continued to kiss, slow and languid as Eddie pulled out and thrust into Dean again, settling into a slow rhythm. 

Their bodies pressed against Dean from all sides, like they were just as wrapped around him as his ass was wrapped around Eddie’s cock. Al’s cock continued to drool precome against Dean’s sweat slick skin. Eddie’s chest hair rubbed over Dean’s nipples. The hair was equal parts soothing, scratching, and stimulating. 

Eddie broke away from kissing Al with a heavy pant. He pressed his forehead to Dean’s cheekbone. His fingers dug into Dean’s hipbones, blunt nails digging into Dean’s flesh as Eddie continued to roll his hips forward. “You feel incredible, babyface.”

“’S’not my name,” Dean said with a grunt. 

Al grabbed hold of Dean’s hair again and tugged his head back until his neck ached in protest. “What was that, boy?”

“I said, that’s not my fucking name,” Dean said with a growl. Whatever drug they’d given him this time might be lighting every erogenous zone and hot spot on his body up like a Christmas tree, but that didn’t mean he had to enjoy getting raped. “Let me go.”

Al snarled. His hold on Dean’s hair tightened to excruciating levels. “Why you little—”

“Al,” Eddie said in a soft voice. Al loosened his grip on Dean’s hair enough that Dean was able to look into Eddie’s eyes. For a man buried balls deep in Dean’s ass against Dean’s will, he was able to pull off the sympathetic friendly look really well. Eddie let one of Dean’s hips go so he could trail his thumb over Dean’s cum stained cheek to his bottom lip. “I tell you what, boy. We will let you go free on one condition. First, I’m going to finish fucking you and I’m going to come deep in this tight little ass of yours. Then Al is going to fuck you and do the same. After that, if I know Al like I do, he’s going to want to eat you out until all of our cum is coating his tongue and cheeks like the frosting on a cake. If you can keep from coming through all of that, we’ll let you go. If not? You’ll be spending the weekend with us.”

Dean swallowed hard. He was literally and metaphorically fucked.

“Deal,” Dean said with a fake cocky smile.

Eddie’s lips twisted into a smile that sent a shiver down Dean’s spine. The kind of smile Dean would normally give to a woman before crawling over her on a motel room bed or the backseat of his Impala. It was the kind of smile that would make Dean a little hot under the collar and send him looking for a fuck or a fight even if he wasn’t drugged out of his mind. Especially if it came from a guy like Eddie. 

“I knew you’d see it my way,” Eddie said with a glint of laughter in his eyes. “Al, sweetheart, would you mind helping me move our sweet boy here to a more comfortable position?”

“Of course,” Al said. He moved his arms from where they were wrapped around Dean’s waist until he could curl his hands over Dean’s shoulders. His forearms braced each side of Dean’s ribcage. His tongue flicked out to tease Dean’s earlobe making Dean’s hands clench and his muscles tighten against the full body streak of pleasure that simple tongue flick sent through him. Al chuckled deep in his chest and whispered against the shell of Dean’s ear. “You have no idea what you’re in for, babyface.”

“Eat me,” Dean said before mentally rolling his eyes at his own choice of words.

Al laughed a little louder this time. “Oh, I will, but not yet.”

Eddie pulled out of Dean’s ass and settled back onto his heels. Dean was momentarily hopeful that the man had changed his mind and was going to let Dean go after all. Then Eddie pushed Dean’s thighs farther apart and wrapped one of his large hands under Dean’s lower back and lifted his hips from the bed like Dean weighed nothing. With his other hand, Eddie lined his cock up with Dean’s ass again. A smile twisted over his lips again as he met Dean’s eyes and pushed slow, slower than before, deep inside Dean again. 

Dean’s eyes rolled back in his head as Eddie pushed deep enough that Dean felt like the inside of his ribcage would be bruised tomorrow from getting fucked like this. 

“Remember, boy,” Al said against Dean’s ear. “You don’t want to come yet.”

“That won’t be a problem,” Dean said, lying to himself as Eddie pulled out and thrust back inside, nailing Dean’s prostate. 

This time, Eddie didn’t take things slow. He fucked Dean like a man starved for it. Al continued to whisper filthy nothings into Dean’s ear as Eddie railed into Dean. Eddie’s cock hit Dean’s prostate almost as often as it didn’t. The sporadic stimulation drove Dean wild and made him curse under his breath and at the top of his lungs. 

Precome leaked from Dean’s cock like faucet. His stomach twitched to prepare for his impending orgasm. Tears burned Dean’s eyes as he finally accepted he might lose this bet. 

In desperation, Dean started conjuring up images of monsters, mutilated victims, and gore from the hunts he’d gone on with his dad. It was the memory of the first time Dean had beheaded a monster with a machete—something that had made him throw up immediately after—that finally made Dean’s cock soften and chased away his orgasm. 

Eddie pounded deep into Dean a few more times and came with a deep, drawn out groan. Dean could feel Eddie pulsing inside his ass. Warmth and the twitching of Eddie’s cock made Dean clench his teeth. 

Thick wetness followed Eddie’s cock as he pulled it from Dean’s ass. Eddie used his thick fingers to work his cum back inside of Dean. 

“Aww, babyface, I don’t know whether to be disappointed in you or proud,” Al said. He moved one of his hands so he could trace his fingers through the slick of precome coating Dean’s stomach. “For a minute there I was sure you were going to come all over yourself untouched like a dirty little boy.”

“In your dreams,” Dean said. His voice sounded as raw and exhausted as he felt. 

“Let’s see if you can pull off the same miracle this time,” Al said. 

Eddie stood up from the bed and settled into a chair next to it so he could watch the two men on the bed. He opened another bottle of water and held it up like he was toasting Dean. “Thanks for that, babyface.”

“Fuck you,” Dean said. 

Eddie cocked his head to the side and pursed his lips between sips of water. “No, I don’t enjoy bottoming. Al might ride you later though. Let you work out some of that frustration.”

Dean was going to say something else witty, but all of his thoughts were interrupted when Al suddenly rolled them and pressed Dean’s face into the sheets. He kept one hand wrapped in Dean’s hair to hold him down and used his other to pull Dean to his knees so his ass was in the air. 

“What the fuck?” Dean managed to get out before Al lined his cock up with Dean’s ass and shoved inside. 

Dean’s eyes widened at the sudden fullness. 

Al groaned in satisfaction. “Oh Eddie…”

Eddie settled back in the chair, spreading his thick thighs. “What’s the matter, sweetheart?”

“Nothing’s the matter,” Al said. “Everything is perfect. He feels incredible, tight. I can feel your cum inside him.”

Eddie hummed. “He takes a load so well. I can’t wait to watch you fill him up. You’ve been waiting so patiently, haven’t you?”

“I have,” Al said. He sounded desperate. 

The fingernails on both of Al’s hands—the one wrapped in Dean’s hair and the one gripping Dean’s hip—dug into Dean’s skin. Dean realized he could feel a tremor in Al’s thighs where they pressed against his own. Dean tried to look over his shoulder at Al when he realized the man hadn’t moved once he’d bottomed out in Dean.

“You want to move, don’t you?” Eddie asked eventually.

“Please,” Al gasped. 

“You think you can make our boy come like this?” Eddie asked thoughtfully. “It would be a shame to lose such a lovely toy so soon.”

“I can,” Al said. “I can make him come like the little slut he’s pretending so hard not to be.”

Eddie hummed skeptically. “I suppose if you’d like to try… go ahead and move, sweetheart.”

It was like a switch was flipped. Al pulled out and fucked forward into Dean with abandon. 

Dean was almost lightheaded from how quickly his cock strained to full hardness again. He bit his lip until his mouth was filled with the metallic tang of blood as Al fucked him brutally. Of course Al would be the rough one. And, of course, Dean’s dick would fail to get the memo that this time he wasn’t supposed to enjoy the rough treatment. 

From deep in his memory, nights he’d spent in other beds with women across the country came to mind. Women who’d tied him down and rode him from dusk until morning. Women who’d used their nails, teeth, and slapping palms to make his toes curl and his back arch. 

Al’s cock skittered over Dean’s prostate.

“Fuck,” Dean cried out. 

“There’s a good boy,” Al said, panting. “Make more of those pretty noises for me, won’t you?”

Dean tried to shake his head as Al continued to aim for Dean’s prostate. Dean’s orgasm started to build up in him again. Tears flowed freely over Dean’s cheeks and he gasped against the sheets as sensation rushed through him. He could feel his cock drooling steadily onto the bed below him. 

At the end of his rope, Dean forced away all thoughts of the beautiful women he’d fucked over the years, and tried conjuring up thoughts that turned him off. When the tang of blood in Dean’s mouth mixed with the sensation of Al fucking into him made his cock twitch at the memory of his first werewolf hunt, Dean knew he was in dangerous territory. 

Desperately, Dean conjured up memories he usually buried. His mother dying, Sam on a bus to California headed for Stanford, Cassie telling him to get the fuck out of her house. It wasn’t until he’d settled on the disappointed disgust on John’s face when he’d found Dean hard in his jeans while he gawked at Han Solo on their old Star Wars VHS tape while Sam was at school and John was supposed to still be away on a hunt, that Dean’s cock finally softened enough for him to be sure he wouldn’t have to worry about coming.

A moment later, Al slammed pelvic bone deep into Dean as he flooded Dean’s ass with cum. 

Eddie clucked his tongue. Dean blinked bleary eyes at him and watched as Eddie shook his head at Al. “Sweetheart, I thought you said you could make this slut come for you.”

Al leaned forward and pressed his forehead to Dean’s shoulder blades. Dean’s cock started to fill again as Al’s softening cock twitched in Dean’s ass. 

“I’m not done with him yet,” Al said before pulling out of Dean’s ass and shoving Dean until he was sprawled out on his back with his legs splayed. Dean could feel the wet spot on the sheets below his ass from where his own cock had leaked a puddle of precome. Al’s fingers petted and curled and scratched over Dean’s stomach and hipbones as Al caught his breath. “Ready to be my midnight snack, babyface?”

Dean swallowed hard.

Al hooked Dean’s thighs over his biceps and folded Dean up so his knees were spread up by his ribs. Al stared at Dean from the other side of Dean’s tightened balls and semi hard cock before he leaned forward and swiped his tongue over Dean’s taint. 

Dean grabbed hold of the sheets. “Oh fuck.”

Eddie chuckled. “If you can hold out against the devilish things Al there can do with his tongue, I won’t just let you go, I’ll give you a fucking medal.”

Al’s pointed tongue had started tracing circles around Dean’s swollen rim by that point. Dean gasped and panted at the sensation. He was too overwhelmed trying to keep his cock from hardening to respond to Eddie’s comment. 

Al’s tongue pushed inside his ass and curled up like a kitten lapping up milk. 

“Holy fuck,” Dean said. 

Dean was vaguely aware of his toes curling in the air over Al’s shoulders, but there was nothing he could do about that as Al sped up his movements. He alternated between circling Dean’s ass, curling his tongue, and sucking at the swollen flesh of Dean’s rim. 

“I told you he was good,” Eddie said. When he’d moved from the chair to where he was now with his elbows resting on the mattress beside Dean and his fingers tracing patterns through Dean’s hair, he didn’t know. Dean blinked up at Eddie, helpless, as he gave up the fight to keep his cock from hardening. It hadn’t done him any good against the sensation of Al eating him out anyway. Eddie smiled softly at Dean, like they were really lovers or something, instead of predators and victim. “Watching you fall apart is quickly becoming one of my favorite things, babyface.”

Dean shook his head. 

Eddie nodded. “It’s true. You’re beautiful like this. All flushed, panting skin. Helpless against the pleasure we’re giving you. It’s gorgeous. I’m so proud of you.”

Dean closed his eyes. His cheeks warmed at the praise. 

Eddie’s beard tickled against Dean’s cheek. “Do me a favor, baby boy?”

“Go to hell,” Dean said, trying valiantly to find that thread of anger that had fueled him earlier. 

“Don’t be like that,” Eddie said. He helped Dean lift his head so that Dean could rest against Eddie’s thick arm. Eddie grabbed Dean’s chin with his thumb and forefinger and tilted Dean’s head down. Eddie’s lips brushed over Dean’s skin. “Open your eyes.”

Much later, Dean would curse his dad for making him follow direct orders without question no matter where they came from, but especially when they came from men with authority over him. Dean opened his eyes just in time to see Al look up from Dean’s hole. Al’s cheeks were glossy with cum and spit. His eyelids were heavy, pupils dilated like tasting Dean was getting him high. He gave Dean a lazy wink and nosed at the underside of Dean’s balls before flicking the tip of his tongue over Dean’s taint again. 

Then Dean was coming. 

His cock pulsed hot cum all the way to his chin with the first wave of his orgasm. Dean stared steadily into Al’s mischievous eyes as he came longer and harder than he could ever remember coming before. Eddie whispered words of praise and adoration in Dean’s ear as the orgasm worked Dean’s body over. Thick white ropes covered Dean’s stomach mixing with hours worth of precome and sweat. Dean’s toes and fingertips started to tingle with the intensity of his orgasm.

When Dean finally stopped coming his body melted against the bed and the two men. They pressed kisses and petted him with gentle hands as they manhandled him until he was stretched out between their naked bodies. 

“We’re going to have so much fun with you this weekend,” Eddie said against the back of Dean’s neck as he cuddled him from behind. 

Dean grunted, sleepy and over-wrung. There was no use fighting it. A bet’s a bet and John Winchester’s son didn’t go back on the consequences of a bet, no matter how bad they were. 

“Do you think we can fit both of our cocks in his hungry little ass?” Al asked as he stroked Dean’s side. 

Dean whined. There was no way he could stretch like that. Eddie petted a hand over Dean’s chest between his raw nipples and shushed him. 

“We can try, sweetheart,” Eddie said. “We’ll let him sleep for now, though.”

Dean blinked heavy eyes as he burrowed down into the warmth coming off the two men. 

“Fine,” Al said. The tone of his voice reminded Dean of Sam when he was little and Dean told him he couldn’t have marshmallows on his nachos. Al leaned in to press a kiss against Dean’s forehead, then his nose, and each of his cheeks. It was almost sweet. 

The world began to fade away as sleep started to take hold of Dean. One of his last memories before he fully succumbed to sleep, was hearing Eddie and Al whisper to each other.

“When he wakes up, I want to watch him ride me,” Eddie said.

“Fuck yes,” Al said. “I want to rim you both while he does. Make sure you pump him full of every drop of cum you build up inside you between now and then.”

“Giddy’up cowboy,” Dean murmured in response as he finally fell asleep. Warm laughter from the two men followed him into his dreams.


End file.
